3-(4-azidobenzoyl)-1,3-thiazolidine-2-thione | 152564-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-azidobenzoyl)-1,3-thiazolidine-2-thione
• 英文别名: (4-Azidophenyl)-(2-sulfanylidene-1,3-thiazolidin-3-yl)methanone
• CAS: 152564-58-4
• 化学式: C₁₀H₈N₄OS₂
• 分子量: 264.332
• InChiKey: YJPXDJFFFBMATA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  92.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-azidobenzoyl)-1,3-thiazolidine-2-thione 、 (E)-2,10-diamino-4-(phosphonomethyl)dec-3-enoic acid semihydrochloride 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以29%的产率得到(E)-2-amino-10-<(4-azidobenzoyl)amino>-4-(phosphonomethyl)dec-3-enoic acid sodium salt
  参考文献：
  名称：

  Synthesis and binding properties of 2-amino-5-phosphono-3-pentenoic acid photoaffinity ligands as probes for the glutamate recognition site of the NMDA receptor

  摘要：

  Four omega-benzoylated (E)-2,10-diamino-4-(phosphonomethyl)dec-3-enoic acids have been synthesized and tested in vitro for binding affinity to the glutamate recognition site of the NMDA (N-methyl-D-aspartate) receptor. The omega-4-azidosalicylamide derivative 24 was iodinated to give the photoaffinity ligand 25 (CGP 55802 A) which showed an IC50 value of 34 nM in the in vitro [H-3]CGP 39653 binding assay. This compound and its radioactive I-125-form are the first photoaffinity ligands for the NMDA receptor with high affinity to the glutamate recognition site.

  DOI：

  10.1021/jm00075a029
• 作为产物：
  描述：

  对叠氮苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 3-(4-azidobenzoyl)-1,3-thiazolidine-2-thione
  参考文献：
  名称：

  Synthesis and binding properties of 2-amino-5-phosphono-3-pentenoic acid photoaffinity ligands as probes for the glutamate recognition site of the NMDA receptor

  摘要：

  Four omega-benzoylated (E)-2,10-diamino-4-(phosphonomethyl)dec-3-enoic acids have been synthesized and tested in vitro for binding affinity to the glutamate recognition site of the NMDA (N-methyl-D-aspartate) receptor. The omega-4-azidosalicylamide derivative 24 was iodinated to give the photoaffinity ligand 25 (CGP 55802 A) which showed an IC50 value of 34 nM in the in vitro [H-3]CGP 39653 binding assay. This compound and its radioactive I-125-form are the first photoaffinity ligands for the NMDA receptor with high affinity to the glutamate recognition site.

  DOI：

  10.1021/jm00075a029

文献信息

• Synthesis and binding properties of 2-amino-5-phosphono-3-pentenoic acid photoaffinity ligands as probes for the glutamate recognition site of the NMDA receptor
  作者：Roland Heckendorn、Hans Allgeier、Jaqueline Baud、Wilfried Gunzenhauser、Christof Angst

  DOI：10.1021/jm00075a029

  日期：1993.11

  Four omega-benzoylated (E)-2,10-diamino-4-(phosphonomethyl)dec-3-enoic acids have been synthesized and tested in vitro for binding affinity to the glutamate recognition site of the NMDA (N-methyl-D-aspartate) receptor. The omega-4-azidosalicylamide derivative 24 was iodinated to give the photoaffinity ligand 25 (CGP 55802 A) which showed an IC50 value of 34 nM in the in vitro [H-3]CGP 39653 binding assay. This compound and its radioactive I-125-form are the first photoaffinity ligands for the NMDA receptor with high affinity to the glutamate recognition site.